2523-42-4Relevant articles and documents
Polyphenol derivatives of porphyrins containing fluorene units: Synthesis and positive-tone photoresists for 22-nanometer lithography
Vainer, A. Ya.,Dyumaev,Kovalenko,Babuskin, Ya. L.,Krichevskaya,Lubenskii
, p. 174 - 178 (2016)
A new strategy was proposed for the synthesis of polyphenol derivatives of fluorene-containing porphyrins to be used as the base for positive-tone photoresists for lithography with exposure at 13.5 nm wavelength, which allow fabrication of microchips with a size of down to 22 nm. Polyphenols based on fluorenecontaining porphyrins were synthesized for the first time. It was shown that these polyphenol derivatives can be used to obtain positive-tone photoresists with a resolution of 22 nm.
Donor-Pi-Acceptor Fluorene Conjugates, Based on Chalcone and Pyrimidine Derivatives: an Insight into Structure-Property Relationship, Photophysical and Electrochemical Properties
Belfield, Kevin D.,Channar, Pervaiz Ali,Irfan, Madiha,Mahar, Jamaluddin,Saeed, Aamer,Shabir, Ghulam,Ul-Hamid, Anwar
, (2020)
A small set of four new fluorenyl chromophores (5-5a-c) was accomplished by stepwise nucleophilic substitution, Friedel-Crafts acylation, Ullman coupling, aldol condensation and cyclization reactions. The fluorene moiety was substituted at 2,7,9 and 9′ positions with diverse groups. The synthesized derivatives were characterized by FTIR, 1H-NMR and 13C-NMR spectroscopic techniques. The optical properties were evaluated by by UV-VIS absorption and Fluorescence studies. HOMO and LUMO energy levels were evaluated by electrochemical studies and were found at ?5.37-5.83 eV and ? 2.47-2.94 eV respectively with band gap energy values 2.88 to 2.91 eV. The band gap energy values suggested that these synthesized molecules can be manipulated in the designing of blue and green OLEDS. [Figure not available: see fulltext.].
An investigation of the effect of conjugation on fluorene based chromophores; Optoelectronic and electrochemical behavior
Mahar, Jamaluddin,Saeed, Aamer,Belfield, Kevin D.,Iqbal, Anila,Irfan, Madiha,Shabir, Ghulam,Larik, Fayaz Ali,Channar, Pervaiz Ali
, p. 385 - 392 (2017)
The requisition of small light emitting organic molecules is on the rise in the field of organic electronics. This study is aimed at synthesis of fluorene based chromophores which possess promising optoelectronic properties. The characterization of synthesized derivatives was carried out by spectroscopy (1H-NMR and 13C-NMR) and spectrometry (EI-MS). The optical properties evaluated by using UV-Vis spectroscopy, were from 394 to 420 nm, Fluorescence ranged 48 nm-113 nm, HOMO energy levels are ?6.75 eV to ?7.15 eV LUMO -4.08 to ?4.52eV with a band gap energy values 2.63–2.67 eV. The band gap energy values suggest that these synthesized molecules can be manipulated in the designing of blue and green OLEDS.
Bio-inspired enol-degradation for multipurpose oxygen sensing
Zhang, Yu-Mo,Wang, Xiaojun,Li, Wen,Zhang, Weiran,Li, Minjie,Zhang, Sean Xiao-An
, p. 13477 - 13480 (2014)
Inspired by the enol-degradation of luciferin, a new oxygen sensor with oppositely changed color and fluorescence has been designed. This new reaction-based dual mode sensor can not only be used as a highly selective instant "fluorescence on" oxygen probe, but also as a freshness indicator of food or food materials by using its property of time-adjustable color fading.
Solid-state construction of zigzag periphery: Via intramolecular C-H insertion induced by alumina-mediated C-F activation
Akhmetov, Vladimir,Amsharov, Konstantin,F?rtsch, Andreas,Feofanov, Mikhail
supporting information, p. 12325 - 12328 (2021/11/30)
Caryl-F bond activation has become an important and quickly developing method for construction of carbon-based materials. We report that alumina-mediated C-F bond activation (AmCFA) enables construction of PAHs with zigzag periphery. This method includes
APEX Strategy Represented by Diels–Alder Cycloadditions—New Opportunities for the Syntheses of Functionalised PAHs
Kurpanik, Aneta,Matussek, Marek,Szafraniec-Gorol, Gra?yna,Filapek, Micha?,Lodowski, Piotr,Marcol-Szumilas, Beata,Ignasiak, Witold,Ma?ecki, Jan Grzegorz,Machura, Barbara,Ma?ecka, Magdalena,Danikiewicz, Witold,Pawlus, Sebastian,Krompiec, Stanis?aw
supporting information, p. 12150 - 12157 (2020/09/01)
Diels–Alder cycloaddition of various dienophiles to the bay region of polycyclic aromatic hydrocarbons (PAHs) is a particularly effective and useful tool for the modification of the structure of PAHs and thereby their final properties. The Diels–Alder cycloaddition belongs to the single-step annulative π-extension (APEX) reactions and represents the maximum in synthetic efficiency for the constructions of π-extended PAHs including functionalised ones, nanographenes, and π-extended fused heteroarenes. Herein we report new applications of the APEX strategy for the synthesis of derivatives of 1,2-diarylbenzo[ghi]perylene, 1,2-diarylbenzo[ghi]perylenebisimide and 1,2-disubstituted-benzo[j]coronene. Namely, the so far unknown cycloaddition of 1,2-diarylacetylenes into the perylene and perylenebisimide bay regions was used. 1,2-Disubstituted-benzo[j]coronenes were obtained via cycloaddition of benzyne into 1,2-diarylbenzo[ghi]perylenes by using a new highly effective system for benzyne generation and/or high pressure conditions. Moreover, we report an unprecedented Diels–Alder cycloaddition–cycloaromatisation domino-type reaction between 1,4-(9,9-dialkylfluoren-3-yl)-1,3-butadiynes and perylene. The obtained diaryl-substituted core-extended PAHs were characterised by DFT calculation as well as electrochemical and spectroscopic measurements.
Preparation method of photoelectric material intermediate (by machine translation)
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Paragraph 0008; 0012; 0013, (2019/10/08)
The invention discloses a preparation method of a photoelectric material intermediate, and is not reported in China at present. To the preparation method provided by the invention, the raw 2 material fluorene -9 is used as a series of operations such as single iodination and the C-N acenyman coupling, crude purification 9 and 9 - the like 4 -2 - 99.0%. The preparation method provided by the invention is simple to operate and suitable for industrial production. (by machine translation)
Synthesis and photophysical properties of new perylene bisimide derivatives for application as emitting materials in OLEDs
Matussek, Marek,Filapek, Micha?,Gancarz, Pawe?,Krompiec, Stanis?aw,Grzegorz Ma?ecki, Jan,Kotowicz, Sonia,Siwy, Mariola,Ma?kowski, Sebastian,Chrobok, Anna,Schab-Balcerzak, Ewa,S?odek, Aneta
, p. 590 - 599 (2018/07/29)
Three novel perylene diimide derivatives with bulky aromatic moieties (fluorene, carbazolyl-fluorene, and anthracyl-fluorene) connected via triple bonds with perylene core were successfully designed and synthesized. The chemical structure of prepared compounds was confirmed by 1H and 13C NMR and mass spectrometry. Their optimized ground-state geometry and frontier molecular orbitals were theoretically estimated based on density functional theory. The compounds undergo the reversible electrochemical reduction process and exhibit very low energy band gaps (1.56–1.98 eV) being promising for electronic applications. They also display excellent solubility, high thermal stability and luminescence in solution and in the solid state as a film in the red spectral region. The highest photoluminescence quantum yield (79% in solution and 28% in the film) was found for perylene diimide bearing fluorene unit. All molecules showed the ability for light emission under an applied voltage. The fabricated diodes with structure ITO/PEDOT:PSS/compound/Al exhibited electroluminescence with maximum emission band located between 685 and 732 nm. The most intense electroluminescence, which was additionally plasmonically enhanced by incorporating silver nanowires, was observed for the device based on molecules with anthracene structure.
4′-Phenyl-2,2′:6′,2″-terpyridine derivatives-synthesis, potential application and the influence of acetylene linker on their properties
Zych, Dawid,Slodek, Aneta,Matussek, Marek,Filapek, Micha?,Szafraniec-Gorol, Gra?yna,Ma?lanka, S?awomir,Krompiec, Stanis?aw,Kotowicz, Sonia,Schab-Balcerzak, Ewa,Smolarek, Karolina,Ma?kowski, Sebastian,Olejnik, Marian,Danikiewicz, Witold
, p. 331 - 343 (2017/07/24)
Novel derivatives of 4'-phenyl-2,2':6′,2″-terpyridine (tpy) with ethynyl (T1), 2-ethynyl-9,9-dioctylfluorene (T2), 9,9-dioctylfluorene (T3), 9-ethynyl-10-decyloxyanthracene (T4) substituents were obtained via Sonogashira or Suzuki-Miyaura coupling reactions, respectively, and thoroughly characterized. The presence of ethynyl bridge impacts photophysical properties of novel compounds by shifting absorption and emission spectra towards longer wavelengths as compared to T3, where fluorene is connected with tpy via a single bond. TGA measurements showed that among the new terpyridines those obtained as solids exhibited high thermal stability as opposed to those which were oils (tpy containing fluorene motif). Due to the fact that high thermal stability of 4'-phenyl-2,2':6′,2″-terpyridine derivatives showed photoluminescence (PL) quantum yield (Φ) in the range of 27–84% in solution, their electroluminescence ability was tested in diodes with guest-host configuration. For the compounds dispersed in a matrix consisting of poly(9-vinylcarbazole) (PVK) (50 wt %) and (2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole) (PBD) (50 wt %) radiation with maxima between 374 and 531 nm and characterized with Φ in the range of 8–12% was observed. They exhibited green or violet electroluminescence. The results confirmed the substantial role of aryl groups and the linker in the presented terpyridines in terms of their thermal, electrochemical, optical and electroluminescence properties. In addition, density functional theory (DFT) and time-dependent-density functional theory (TD-DFT) calculations were performed to provide an independent support and deeper insight into the experimental results.
Design, synthesis, and evaluation of potent Wnt signaling inhibitors featuring a fused 3-ring system
Xu, Zhixiang,Li, Jiajun,Wu, Yiyuan,Sun, Zhijian,Luo, Lusong,Hu, Zhilin,He, Sudan,Zheng, Jiyue,Zhang, Hongjian,Zhang, Xiaohu
, p. 154 - 165 (2015/12/04)
The Wnt signaling pathway is a critical developmental pathway which operates through control of cellular functions such as proliferation and differentiation. Aberrant Wnt signaling has been linked to the formation and metastasis of tumors. Porcupine, a member of the membrane-bound O-acyltransferase family of proteins, is an important component of the Wnt pathway. Porcupine catalyzes the palmitoylation of Wnt proteins, a process needed for their secretion and activity. Here we report a novel series of compounds obtained by a scaffold hybridization strategy from a known porcupine inhibitor class. The leading compound 59 demonstrated subnanomolar inhibition of Wnt signaling in a paracrine cellular assay. Compound 59 also showed excellent chemical, plasma and liver microsomal stabilities. Furthermore, compound 59 exhibited good pharmacokinetic profiles with 30% oral bioavailability in rat. Collectively, these results strongly support further optimization of this novel scaffold to develop better Wnt pathway inhibitors.
